Chromium compounds of azo dyestuffs



t No Drawing.

tin-arse S ATE-s Josnrn cnmmnn. ms FRITZ castes.

smun, or mean, swrrznrmelm, ASSIGN'ORS 'ro SOCIETY OF GHEMICAL INDUSTRY IN BASLE, OF BASEL, SWITZERLAND.

. OHROM IUM COMPOUNDS AJZO DYESTUFFS.

incense;-

' Toallaqh'om it may vented new and useful -Chron 1iunr+Com-'" pounds of Azo Dyestufi's, of whlch the folh Be it known that we, Josnrn GmMMER, a

citizen of the Czecho Slovak Republic, and

resident 'of Basel, Switzerland, and FRrrz STRAUB, a .citizen of the Swiss Republic, and

resident of Basel, Switzerland," have inlowing is a fpll, clear, and exact specification e J We have found that new mordant dyeing dyestuffs are obtained by combinig the diazoderivative of a 1-amino-2-oxynaphtha 1ene-4-sulfonic compound with a. halogen substitution product of .alphanaphthol. These dyestuffs dye wool in an acid bath red- *violet tints, which by after-chroming become rey to blue and by *after-coppering Y -1018i.

y treating, these'dy'estufi's correspondlngto the general formula R N=N'- R (wherein RN=N+ designates a 1-diazo'-2-.oxynaphthalene l-sulfonic' compound-and R a halogenatedalphanaphthol) further with agents yielding chromium, chromium compounds are obtained which are also new dyestuflt's'of valuable properties. These chromium com;

pounds constitute dark powders, which diss'olve'in water with blue'to greenish black colorations and in concentrated sulfuric acid with greenish blue to violet colorations and give on wool, when ,dyed according to the manner employed for acid dyestufi's, very fast,-green-blue to grey tints.

' The invention is illustrated by the following examples: i p j a, I Ewamplel. L

'89" arts of l oxy 8-chloronaphthalene are diSSOl ed in an excessof caustic soda lye and mixed at a lowjte'mperature with an aqueous suspension of 130. parts ofydiazotized 1- amino-2-oxy-naphthalene 4 P sulfonic I acid. The mixture isstirred until the diazo-compound has disappeared, diluted with water and neutralized with hydrochloricv acid, whereupon the dyestufi is salted out.

The new dyestufi forms a dark powder having a weak metallic lustre. It produces red-violet tints on wool, which becomes into .1000 parts 'of an 1 parts of caustic soda and 112.5 parts of p with mineral acid and the chromiferous dye-- g oolin an acid bath .very equal,

ment which maybe present.

specification of Letters Patent. iPatent ed JamB, 1922., Application filed April 15, 1921. SerialNo. 461,588. a

greenish blue when after-chromed and blue v olet when after-copp'eied.

428.5 parts of this dyestufi are introduced aqueous solution conta1n1ng-76.5 parts of chromium oxid, 224 glycerine, ours in'a refluxapparatus. The mixture is now diluted with three times its weight of water, the liberated alkali is neutralized stufl issalted out, filtered and dried. It forms, when 'dry, a dark powder. v green=blue n}? fast to fulling and eminentlyfast to;

, mctmple 2., y

' 213 parts of 1-oxy-5 :8-dichloron'aphthalene are dissolved in a mixture of .400 parts of 'water and 40 parts of caustic soda; the solution is mixed with into it is introduced an aqueous, suspension of 305 parts of the nitro-compound of the diazotized': 1-amino-2-oxy-naphthalene--sub fonic acid. .fihe mixture -is stirred, care being taken that the temperature does not rise above 10 C. As soon as thedia'zo-comchromium corresponding with 36.8 per cent of C130 in all 114.7 arts of Cr O and .612 parts of crystallized sodium acetate; the mixture is boiled in a reflux'apparatus for 7 hours, and is then filtered from any sedi- The filtrate is evaporated to half its volume, the chromium compound is precipitated by adding and the whole is boiled for" 10 It dyes 7oa solution of parts I of caustic soda 1n 200 parts of water and equal grey tints, fast to fulling and eminently fastto light.

dark neoaeec amino-Q-oxy naphthalene-4=-sulfonic acid.

phachlorinatedalphanaphthol) with Coloration oi the solu- Tint o! the chromium e Coloration of the solu- Dlazotized-com onent. Cou lln com onent. tmn in concentrated com ound on wool p p p mmmwatersulturicacid. (aci dyes).

Diazotlzed acid 1-Oxy-8-chloronaphtliulene. Blue Blue Grcen'hlue. Chloro-diazotized acid 1-Oxy-8chloronaphthalene. Blue Blue Greenblue. .Bromo-diazotized acid..... 1-Oxy-8-ch1oronaphthalene. Blue. Greenishblue Greenblue.

Nitro-diazotized acid l-Qxy-tchlorona hthalene. Greemsh black-1 Violet Grey. Diazotlzed acid............. 1-?hxy -5: B-dich oronaph- Bl e Blue Gteenblue. acne. I

Chloro-diazotizedacid Iggy-5: B-dichloronaph- Blue Greemsh' blue.............. Green blue.

P aene. .Bzomo-diuzotizedecid..... l-jghxyiz B-dichloronaph- Blue Bluemi Gteenblue.

, i acne. Nitrodiozotized acid l-gfypm adichloronaph Greemsh black Violet Grey. I eene.

What we claim is: I

'1. The herein described new. chromium compounds resulting from the treatment of the new mordant d ein d estufi of the eneral formula (wherein h N=N- signifies a 1-diazo-2-oxynaphthalene-d-eultonic compound and R a halogenated alphanaphthol) with an agent yielding chromium, which constitute dark. powders soluble in water with blue to greenish-black and in concentrated sulfuric acid with greenish-hlue to yioletcolorations and dye wool,

employed for acid dyestutls, very equal and verydast blue to grey-tints.

2. The herein described new chromium compoundsresultin from the treatment of thegnew mordant eneral formula R-N=N-R, (wherein -N N signifies a 1-diazo-2-oxynaphthalene-d-sulfonic' compound and R an allan agent yielding chromium, which constitute owders-soluble in water with blue to green sh-lolackand in concentrated sulfuric acid with greenish-blue to violet colorations and tlye wool, when dyed according to the new mordant dyeing digestufis of the manner usually employed for acid dyestufis, very e ual and very fast blue to grey tints.

8. T e herein described new chromium compounds resulting from the treatment of the formula ,R-N:N (wherein N: N- signifies a.1-diazo-2=oxynaphthalene-dsulfonic compound. and R analphadichlo rinated alphanaphthol) with an agent yield- 1 ing chromium, which constitute ark powders soluble in water with blue to greenishblack and in concentrated sulfuric acid with greenish-blue to violet colorations and dye yeing dyestufis of the eneral usua ly employed for-acid dyestufi's, very equal and very fast blue to grey tints.

4. The herein described new chromium compounds resulting from. the treatment of the new mordant d ein estufi's' of the en-. eral formula R- ll=-%V, ,(wherein NzN- signifies a 1-diazo-2-2oxynaphthalene-d-sulfonic compound and -R 5:8-dichloro-alpha-naphthol) with an agent yielding chromium, which constitute dark powwooli when dyed according to the manner I ders soluble in water with blue to greenishblack and in concentrated sulfuric acid with greenish-blueto violet colorationsand dye wool, when dyed according to the manner usually employed for acid dyestufis, very equal and very fast blue to grey tints;

5. The herein described. new chromium compounds resultin from the treatment of the new mordant dyeing dyestuffs of the general formula R-N:=N R,' (wherein iRfiN=N-- signifies a nitro-l-diazo-2-oxynaphthalene-l-sulfonic acid and B 5:8-dichoroalpha-naphthol) with an agent yield-' ing chrommm, which constitute dark powderssoluble in water withgre enish-black col-- orat1on and in concentrated sulfuricv acid with violet coloration and dye wool, when dyed accordin to the manner usually employed for acid dyestuffs, very equal and verly fast grey tints.

witness whereof we have hereunto signed. our namesthis 1st day of April, 1921,

in the presence of two subscribing witnesses. JOSEPH GRIMMER. v FRITZ STRAUBQ Witnesses! I FnmA Kunz, AMAND 

